反応 #2430

反応方程式

Methyl(3-amino)benzoate

4-Pentenoyl chloride

4-pentenoic acid

thionyl chloride

→

oil

収率 32.0%

Methyl 3-(4-pentenoylamino)benzoate

収率 32.0%

溶媒

pyridine

DCM

反応条件

後処理

1. 1
   その他at 0° C
2. 2
   その他evaporated
3. 3
   その他azeotroped with DCM)
4. 4
   workup.ADDITIONwas added dropwise in DCM (3 ml)
5. 5
   その他The mixture was evaporated
6. 6
   その他partitioned between EtOAc and 1M HCl
7. 7
   洗浄The organic portion was washed with 5% KHCO3 and brine
8. 8
   ろ過filtered (Whatman® 1PS, phase separator)
9. 9
   その他evaporated
10. 10
    その他The residue was chromatographed (eluant 30% EtOAc in hexanes)

実験手順

Methyl(3-amino)benzoate (4.5 g, 29.8 mmol) was taken up in DCM (10 ml) and pyridine (1 ml) at 0° C. 4-Pentenoyl chloride (freshly prepared from 4-pentenoic acid (3.0 g, 29.97 mmol) and thionyl chloride (6.6 ml) at r.t. for 1 h, evaporated and azeotroped with DCM) was added dropwise in DCM (3 ml). The mixture was allowed to warm to r.t. and stirred overnight. The mixture was evaporated and partitioned between EtOAc and 1M HCl. The organic portion was washed with 5% KHCO3 and brine, filtered (Whatman® 1PS, phase separator), and evaporated. The residue was chromatographed (eluant 30% EtOAc in hexanes) to provide a colourless oil (2.20 g, 32%).

出典